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Jackie always had a weakness for Jenny and protected her in the orphanage, often taking a beating for her. When she realized Jackie was a hitman and bearer of the Darkness she left Jackie. It was too painfull for her to look at Jackie living his life this way, especially since she had feelings for him.
Jenny appears in the video game version of The Darkness. She is Jackie's girlfriend ever since they were in the same orphanage as kids. They even celebrated his 21st birthday. Jackie tries to tell Jenny that he is a hitman working for Uncle Paulie, but she doesn't believe him. Later, she is kidnapped by Paulie and crooked cop, Captain Eddie Shrote, and is taken in the same orphanage where she and Jackie used to go. While on a mission to rescue her, the Darkness holds Jackie back from doing the rescue, giving Paulie a chance to kill her in front of him. Before she died, Jenny said to Jackie that it is not his fault they got into this situation.
She reappears in the sequel as an apparition to Jackie. Later in the game, she appears in Hell taken hostage by the Darkness. When Jackie tries to save her, the Darkness warns him not to do it. After the rescue, the two hug briefly before Jenny flies out of his arms and transforms into the Angelus
. This is the reason why the Darkness has taken her; it knows that she will become the new host. Jackie demands to give Jenny back, but the Angelus said that she's still inside her, and despite everything he has done, she still loves her. He refuses to fight her and the Angelus tells him that he and the Darkness are now trapped in Hell forever before flying away.